Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/54—Three nitrogen atoms
  • C07D251/70—Other substituted melamines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
  • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
  • C09B62/08—Azo dyes
  • C09B62/09—Disazo or polyazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0083—Solutions of dyes

Definitions

• the sum of the basic and cationic groups is greater than the number of sulfonic acid groups, since each sulfonic acid group can form an inner, sparingly soluble salt with a basic or cationic group.
• the additional basic (s) or cationic (s) group (s) can be localized in D, M, A and Z.
• Halogen is especially fluorine, chlorine or bromine.
• Alkyl is preferably C 1 -C 4 -alkyl, alkoxy for C1-C4-alkoxy, arylene for phenylene or naphthylene and aryl for phenyl or naphthyl.
• the diazo or tetrazo components must be selected in such a way that the condition of water solubility is met, i.e. that the resulting dye molecule contains at least one basic or cationic group more than the molecule has sulfonic acid groups.
• an aromatic carbocyclic or heterocyclic diazo or tetrazo component - which is free of anionic groups - such as aniline, aminoazobenzene, Aminonaphthalene, 4,4'-diamino-benzoyl-anilide, 4,4'-diamino-3,3'-dimethyl- or dimethoxydiphenyl, 4,4'-diaminodiphenylethane (1,2) are used.
• the aromatic carbocyclic or heterocyclic diazo or tetrazo component must have at least one basic or cationic group in order to achieve water solubility.
• Suitable diazo components of this type are, for example: aniline-3- or -4-trimethylammonium chloride, sulfate, methosulfate, tosylate, benzene sulfonate, 3- or 4-amino-benzyldi or trimethylammonium chloride, methosulfate or 2-aminonaphthalene 5-methylene trimethyl ammonium methosulfate.
• amino azo compounds with ammonium groups which are bonded via a methylene group such as 4-aminoazobenzene-4'-dimethylammonium or trimethylammonium chloride, 4-amino-azobenzene-3'-trimethylammonium chloride, 4-amino-azobenzene chloride 4'- or 3'-methylenetrimethylammonium chloride and in the benzene nucleus these azobenzenes in the 3- or 2-position by methyl, methoxy, ethoxy, chlorine-substituted compounds such as 2-aminonaphthalene-5-methylene-trimethylammonium chloride ⁇ aniline or ⁇ 3-methylaniline or ⁇ 2-methoxyaniline.
• amino azo compounds with ammonium groups which are bonded via a methylene group such as 4-aminoazobenzene-4'-dimethylammonium or trimethylammonium chloride, 4-amino-azobenzene-3'-trimethylammonium chloride, 4-a
• cyanuric halide preferably chloride or fluoride
• the individual condensation steps can be interchanged and, for example, the amino compound (XIII) first be condensed with the cyanuric halide.
• Examples of the compounds HZ are: C 1 -C 4 -mono- or dialkylamines such as methyl, ethyl, chloroethyl, propyl, isopropyl, butyl, hydroxyethyl, 2-methoxy ethyl, dimethyl, diethyl, di-i-propyl, di-n-propyl, diethanol, di-iso-propanol, di-isobutyl, methyl-ethyl, methyl-ethanol and ethyl ethanolamine, 3-methylaminopropanitrile, cycloalkylamines such as piperidine, morpholine, piperazine, methylpiperazine, hydroxyethylpiperazine, aralkylamines such as benzylamine, benzylmethylamine, benzylethanolamine, which can be substituted in the phenyl nucleus by chlorine or methyl.
• Diamines such as ethylenediamine, N, N'-dimethylethylenediamine, 1-amino-2-diethylaminoethane, propylenediamine, N-methyl- and N, N-dimethyl- or ethyl-propylenediamine, dipropylenetriamine, diethylenetriamine, N, N ', N "-trimethyldiethylenetriamine , 1,4-diaminocyclohexane.
• Aromatic amines such as aniline, N-methyl or ethyl- or hydroxyethyl-aniline, which are in the phenyl nucleus in the o-, m- or p-position by methyl, ethyl, chlorine, methoxy, ethoxy, N, N-dimethyl- or N, N -Diethyl-amino, trimethylammonium- chloride, methosulfate or acetate, methylenedimethylamino or methylenetrimethylammonium methosulfate may be substituted, 1-naphthylamine, dehydrothiotoluidine or xylidine, 2-amino-benzothiazole, 3-aminoisobenzothiazole, 2-aminonaphthalene-5-methylenetrimethylzinium and dimethylchloride.
• Suitable amino compounds (XIII) are, for example: (chloride, bromide, methosulfate, tosylate, benzenesulfonate being preferred as anion A (-) )
• the dyes are used for dyeing materials which can be dyed with cationic dyes. Examples include: polyacrylonitrile, acid-modified polyesters, for example polyglycol terephthalates, as described in Belgian patent 549 179 or US Pat. No. 2,893,816, acid-modified polyamides, tannic vegitabil fibers (cotton), leather and preferably paper.
• the dyes are suitable for dyeing sized and sized paper, it being possible to start with bleached or unbleached cellulose and to use deciduous or softwood cellulose such as birch and / or pine sulphite and / or sulphate cellulose.
• the dyes are used both as powder or granule preparations and in the form of concentrated solutions.
• Powder preparations are made in the usual way with setting materials such as sodium sulfate, phosphate, chloride, acetate in the presence of dustproofing agents, or the dyes are marketed directly as spray-drying preparations.
• Concentrated dye solutions can be of an aqueous or aqueous / organic type, with customary, environmentally friendly and as easily degradable additives as preferred, such as organic acids, preferably acetic acid, formic acid, amides such as formamide, dimethylformamide, urea, alcohols such as glycol, diglycol, diglycol ether, preferably its methyl or ethyl ether.
• the dyes have excellent drawability and very good general fastness properties. Paper dyeings are characterized by very good wet fastnesses as well as alum, acid and alkali fastnesses. They have a surprisingly high light fastness, with high clarity and color strength.
• the second condensation component is the solution of 18 parts of aniline-3-trimethylammonium chloride (volume approx. 70 parts), heated to 40-50 ° C., the pH is kept at 5-6 by dropping 20% sodium carbonate (soda) solution and stir until the ammonium compound is no longer detectable (test by diazotization and coupling for R salt solution).
• the monochloro compound obtained is in solution after the condensation has ended.
• the coupling component of the formula is present before, which is adjusted to pH 2 by acidification with 28% hydrochloric acid and can be further processed directly in this acid / salt form or is isolated in the usual manner, for example as a double zinc salt.
• the I-acid is used as the first condensation component, condensed as above at 0 to 5 ° C. with cyanuric chloride, it is expedient to carry out after the 2nd condensation stage at 40-50 ° C. with aniline or N-methylaniline, 2-methylaniline, methylamine, Dimethylamine, N, N-dimethylpropylenediamine or other amines HZ mentioned above are intermediately isolated and finally condensed in a third stage at 80-95 ° C. with aniline-3-trimethylammonium chloride or acetate, for example to form the coupling component
• the coupling component is obtained, for example
• the hydrochloric acid solution of 25 parts (0.1 mol) of 2-aminonaphthalene-5-methylenetrimethylammonium chloride (volume approx. 70 parts) is in the usual way after adding about 100 parts of ice with 24 parts of 30% aqueous sodium nitrite solution at 0 ° C diazotized.
• the diazonium salt remains in solution. Shortly before coupling, excess nitrous acid is destroyed with sulfamic acid.
• the precipitated dye is isolated and dried. It then represents a dark powder that dissolves in water with a red color.
• the precipitated dye of the coupling batch is adjusted to pH 12 with 40% sodium hydroxide solution, the dye is isolated and the dye paste obtained is dissolved in 120 parts of 50% acetic acid at about 50 ° C. and clarified from minor residues.
• the resulting, cold-stable red dye solution dyes paper according to the usual dyeing processes (with or without the addition of glue) in intense red tones (No. 7).
• the dye has good wet fastness properties.
• the coupling components 1, 2 or 1.3, 1.8, 1.9, 1.10, 1.11, 1.14, 1.15, 1.19, 1 are used as the coupling component, 20, 1.27, 1.28, 1.30, 1.31, one obtains dyes with the above diazo components which dye paper in shades similar to those with the above coupling component 1.5.
• the hydrochloric acid solution of 0.1 mol of the coupling component of Formula 1.1 (volume 500 parts) is cooled with ice to 0 ° and with the prepared in a conventional manner solution of 0.1 M 4-ol Chlorbenzoldiazoniumchlorid (volume 230 parts) were combined. 20% sodium acetate solution is then added dropwise to pH 4-5 and the mixture is stirred until the coupling is complete.
• the dye of the formula is isolated in the usual way and either dried or a dye solution is prepared with 50% acetic acid. The dye dyes paper in orange tones (No. 6).
• aniline 4-aminotoluene, 2,4- or 2,5-dichloroaniline or aniline-3-trimethyl-ammonium chloride- is used as the diazo component instead of 4-chloroaniline, orange-colored dyes are obtained (I.No. 5-6 ).
• diazo components 4-methoxyaniline, 2-methoxyaniline, 4-ethoxyaniline (No. 8), 2- (4-aminophenyl) -6-methylbenzothiazole, 2- (4-aminophenyl) -4,6-dimethylbenzothiazole, 2- (4-aminophenyl) -benzimidazole (I.No.

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• 1981
  • 1981-04-08 DE DE19813114087 patent/DE3114087A1/de not_active Withdrawn
• 1982
  • 1982-03-29 DE DE8282102617T patent/DE3275646D1/de not_active Expired
  • 1982-03-29 EP EP82102617A patent/EP0062825B1/fr not_active Expired
  • 1982-04-02 JP JP57053965A patent/JPS57179171A/ja active Granted
• 1984
  • 1984-11-13 US US06/670,683 patent/US4839468A/en not_active Expired - Fee Related

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